(S)-1-azido-3-bromo-2-propanol

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: (S)-1-azido-3-bromo-2-propanol
• 英文别名: (2S)-1-azido-3-bromopropan-2-ol
• 化学式: C₃H₆BrN₃O
• 分子量: 180.004
• InChiKey: MATJBGYRKJDRBU-GSVOUGTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  环氧溴丙烷 在 sodium azide 、 sodium acetate buffer 、 Agrobacterium radiobacter AD₁ haloalcohol dehalogenase 作用下， 生成 1,3-二溴-2-丙醇 、 (R)-2-(溴甲基)环氧乙烷 、 (S)-1-azido-3-bromo-2-propanol 、 (R)-1-azido-3-bromo-2-propanol
  参考文献：
  名称：

  Enzymatic dynamic kinetic resolution of epihalohydrins

  摘要：

  The haloalcohol dehalogenase from Agrobacterium radiobacter AD1 catalyses the reversible ring closure of vicinal haloalcohols to produce epoxides and halides. In the ring opening of epoxides, nonhalide nucleophiles such as N-3(-) are accepted. The enantioselective irreversible ring opening of an epihalohydrin by N-3(-), combined with racemisation caused by a reversible ring opening by a halide, resulted in an enzymatic dynamic kinetic resolution yielding optically active (S)-1-azido-3-halo-2-propanol. With epichlorohydrin as a substrate, the rate of ring opening by N-3(-) was higher than the rate of racemisation, resulting in a mixed kinetic resolution and dynamic kinetic resolution. With epibromohydrin as the substrate, the racemisation rate was higher than the rate of ring opening, resulting in an efficient dynamic kinetic resolution. By optimising the pH of the medium and the concentrations of N-3(-) and Br-, the product (S)-1-azido-3-bromo-2-propanol could be obtained in 84% yield and 94% ee. An (R)-enantiomer selective ring closure of this bromoalcohol, catalysed by the same enzyme, caused a simultaneously occurring kinetic resolution, yielding when the conversion progressed, an increase in enantiopurity of (S)-1-azido-3-bromo-2-propanol to >99% ee with a yield of 77%. This compound and the ring-closed product glycidyl azide can be used as chiral synthetic building blocks. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.02.009

文献信息

• Enzymatic dynamic kinetic resolution of epihalohydrins
  作者：Jeffrey H Lutje Spelberg、Lixia Tang、Richard M Kellogg、Dick B Janssen

  DOI：10.1016/j.tetasy.2004.02.009

  日期：2004.4

  The haloalcohol dehalogenase from Agrobacterium radiobacter AD1 catalyses the reversible ring closure of vicinal haloalcohols to produce epoxides and halides. In the ring opening of epoxides, nonhalide nucleophiles such as N-3(-) are accepted. The enantioselective irreversible ring opening of an epihalohydrin by N-3(-), combined with racemisation caused by a reversible ring opening by a halide, resulted in an enzymatic dynamic kinetic resolution yielding optically active (S)-1-azido-3-halo-2-propanol. With epichlorohydrin as a substrate, the rate of ring opening by N-3(-) was higher than the rate of racemisation, resulting in a mixed kinetic resolution and dynamic kinetic resolution. With epibromohydrin as the substrate, the racemisation rate was higher than the rate of ring opening, resulting in an efficient dynamic kinetic resolution. By optimising the pH of the medium and the concentrations of N-3(-) and Br-, the product (S)-1-azido-3-bromo-2-propanol could be obtained in 84% yield and 94% ee. An (R)-enantiomer selective ring closure of this bromoalcohol, catalysed by the same enzyme, caused a simultaneously occurring kinetic resolution, yielding when the conversion progressed, an increase in enantiopurity of (S)-1-azido-3-bromo-2-propanol to >99% ee with a yield of 77%. This compound and the ring-closed product glycidyl azide can be used as chiral synthetic building blocks. (C) 2004 Elsevier Ltd. All rights reserved.